Q&A: "Should I quit my job when the economy is bad?"

A listener wants to know: "With the downturn in this economy, should I quit my job?"

I've been hearing from a lot of people in a time of transition one way or another. It's good to go case-by-case and look at different examples—one individual often serves as a proxy for lots of people who are wondering the same thing.

Side note: when you send me these questions, include some detail about your business so I can be more helpful. But I think I still have a good general answer with some questions you can ask yourself when facing this issue.

Hi, Chris. This is Sanjay from New York. I'm listening to the show for a while now and this is my first chance actually to ask a question. So I was about to make a leap from a corporate job to something more independent, kind of striking out on my own. I was very excited about it, but now I'm a little torn with everything that's going on. On the one hand, I'm thinking of making a move like this seems incredibly risky and maybe even a little foolish at a time like this when the economy is doing so poorly. But on the other hand, I recognize there's never really a good time to take a leap of faith. And sometimes down moments are actually when the greatest opportunities arise. So I'm just curious if you have any thoughts or perspective for how do I think about that and determine if this is the right time?

I think it all has to do with your situation, specifically relating to the side hustle/business itself.

You didn't mention what that is, and that to me is the critical point: is it going well, is it providing a sustainable level of income, and (crucially!) is it the kind of business that will be able to thrive in this new environment?

If yes, great. If no, probably not a good idea to go all-in right now.

Let's take a few extreme examples…

If your business is a travel agency, not a good idea to go all-in, even if it was working before. Yes, people will eventually travel again, but it will be a while, and they will come back slowly, and the entire industry will be struggling for a long time.

If your business is training for corporate remote employees, and you already have existing contracts plus sales contacts you're working on, this is probably a really good time.

In this environment, it really is key to ask that additional question about what's going on now because it is affecting so much and I don't want you to make the wrong decision.